Sodium Hydroxide → 4-(4-Fluorophenyl)cyclohexan-1-one

HRID 432599Notes

Reaction equation

HRID 432599 reaction equation
O1C2(CCC(N3CCN([C:17]4[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=4)CC3)CC2)OCC1.[OH-:24].[Na+]>Cl.O1CCOCC1>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH:17]2[CH2:22][CH2:21][C:20](=[O:24])[CH2:19][CH2:18]2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18760058Piperazine, 1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-(4-fluorophenyl)-

Product 1

HCID 128343224-(4-Fluorophenyl)cyclohexan-1-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(1,4-dioxa-spiro[4.5]dec-8-yl)-4-(4-fluoro-phenyl)-piperazine (3.13 gm) (C18H25FN2O2) in 100 ml 3N hydrochloric acid and 100 ml dioxane was stirred at ambient temperature for 2 hours. The mixture is cooled to 0° C., neutralized with 2N sodium hydroxide and extracted with 2×100 ml ethyl acetate. The ethyl acetate layer was washed with water and brine (each 2×40 ml), dried over sodium sulfate and concentrated to a solid. This material, which was recrystallized from ethyl ether (1.5 gm), has a melting point of 104-106° C.

Workup

  1. extractionextracted with 2×100 ml ethyl acetate
  2. washThe ethyl acetate layer was washed with water and brine (each 2×40 ml),
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to a solid
  5. customThis material, which was recrystallized from ethyl ether (1.5 gm)

Sources & evidence

ORD record
ord-61714101948e4c11ab8152f6defafcce
Source dataset
uspto-grants-2003_12
Patent number
US06664258B1

Reaction notes

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